This invention relates to 2-(heterocyclic)phenyl sulfamates which are useful as agricultural chemicals.
U.S. Ser. No. 261,751 teaches that o-alkylsulfonyloxysulfamates are herbicidal.
DE No. 3,105,453 assigned to Hoechst AG teaches that phenoxysulfonylureas are herbicidal.
Netherlands Patent No. 121,788, published Sept. 15, 1966, teaches the preparation of the following compounds and their use as general or selective herbicides: ##STR1## wherein
R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.
French Pat. No. 1,468,747 discloses para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR2## wherein
R.dbd.H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR3## wherein
R is butyl, phenyl or ##STR4## and
R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
U.S. Pat. No. 4,191,553 discloses herbicidal compounds of the following formula: ##STR5## wherein
R.sub.1 is H, OCH.sub.3 or alkyl or 1-3 carbons;
R.sub.2 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, CF.sub.3 or ##STR6##
R.sub.3 is H, Cl, F, Br, CH.sub.3, or alkoxy of 1-4 carbons;
R.sub.4 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, CN or ##STR7##
R.sub.5 is H, Cl, F, Br, CH.sub.3, NO.sub.2 or CF.sub.3 ;
R.sub.6 is H, Cl, F, Br, alkyl of 1-4 carbons or alkoxy of 1-4 carbons;
R.sub.7 is Na.nu.O-, OH, or alkoxy of 1-4 carbons;
X is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S, CH.sub.3 CH.sub.2 S, CF.sub.3 or Cl;
Y is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S or CH.sub.2 CH.sub.3 S; and
Z is CH or N;
provided that
only one of R.sub.2, R.sub.3 or R.sub.4 is alkoxy; and
when R.sub.5 is NO.sub.2, R.sub.4 is other than NO.sub.2.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR8## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.